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Much of the literary criticism on Kate Chopin’s The Awakening has focused upon the main character, Edna Pontellier, and her journey of self-discovery, but the surrounding cast is rich with personalities as diverse and enlightening as Edna’s own. While most of the characters seem clearly defined as to their values, desires, and how they reconcile any dissonance they might face, and Edna Pontellier might seem like the only person suffering the torment of this discord, each character is actually negotiating a careful playing field replete with rules, regulations, and strict penalties if one is to run afoul. This essay explores the function gender roles play with regard not to the women in the story, but to the men. The events in the story show how the sociocultural demands and expectations placed upon the men are equally as divisive as those placed upon the female characters of the same social status in this upper middle class, Creole, white community. The shackles which constrained men and women, particularly the Creole folks with whom Chopin interacted most, were being stretched to their limits, and it was only a matter of time before they shattered under the stress of social progress. This novel is an important benchmark in the timeline of America both for its depiction of southern Creole values, but also the delicate balance of the gender binary which was about to be disturbed by the Women’s Suffrage movement. By challenging this limiting status quo, Chopin proves a keen observer of the harm resulting from these restrictions and the liberating quality of their abolition.